Media’s Hottest Dealmaker on How to Negotiate, Mastering the Calendar to Create More Time, and More

Aryeh Bourkoff traces his path from putting resumes under windshield wipers in 1995 New York to advising on some of media's largest deals, including selling MGM Studios to Amazon. He explains the foundations of being a strong research analyst, the discipline of holding a 'strong core' while operating in the gray area, and how he engineered extra time by holding Wednesday 10pm-2am office hours in LionTree's first year. He shares hard-won negotiation philosophy built on meeting the other side where they are and on trust, illustrated by the MGM impasse and the famous deck-of-cards fee story with CBS's Joe Ianniello. He closes with his outlook on the audio and podcasting market, predicting more curation, branding, monetization, and cross-asset use of podcast personalities by platforms like Amazon and Spotify.

• Bourkoff describes his competitive advantage as comfort in the 'gray area' he can stay in longer than most until he sees the optimal moment to act.
  00:31:28
• To solve the problem of a full calendar in LionTree's first year, he created an extra 'day' by holding external office hours every Wednesday from 10pm to 2am, eating into his sleep.
  00:37:32
• He reveals the 2007 sale of the Sundance Channel to the Dolans/Cablevision for $500 million, noting Robert Redford likely made more than from all his acting years combined.
  00:58:09
• The deck-of-cards story: CBS treasurer Joe Ianniello rigged an entire card-trick negotiation so Bourkoff repeatedly drew a three, setting their fee at $3 million.
  01:00:16
• His core negotiation lesson: 90 percent of people focus on what matters to them, but all that matters is how it lands to the other person, so you must meet them where they are.
  01:03:36
• He recounts selling MGM Studios to Amazon for around $8.5 billion, breaking a months-long $8B-vs-$9B impasse by being given the chairman's proxy to split the difference under a 24-48 hour counteroffer condition.
  01:08:53
• On rejecting 40 of 45 deals at UBS as the balance-sheet 'goalkeeper': he played the long game, betting more shots on goal would come and refusing to chase negatively-selected, lower-quality companies.
  01:32:41

• Bourkoff founded LionTree in 2012 and was ranked the number one cable and satellite analyst by Institutional Investor for seven consecutive years.
  00:00:15
• His first New York job interview was for an oil-and-gas analyst role with Paul Ting at Oppenheimer in 1995, which fell through over a Visual Basic requirement; years later he welcomed Ting as a UBS hire and told him he'd mastered the language.
  00:16:00
• Mentor Alan Ginsberg, who hired him at Smith Barney, had written for Rolling Stone and once chided him for reading only the financial numbers and not noticing the Florence opera house had burned down.
  00:11:04
• He chose ending office hours at 2am citing a U2 song ('Hawkmoon 269' from Rattle and Hum) about the magic hours when it's not yet morning but past everyone's nighttime.
  00:41:54
• He recommends three timeless books: 'Leadership and Self-Deception,' 'Scale' by Geoffrey West, and 'Scarcity.'
  01:13:13
• He was reading 'A Banker's Journey' about Edmond Safra and a Chris Blackwell book on the music industry, and looked forward to Jann Wenner's new book.
  01:16:35
• He praises David Brooks' 'The Second Mountain' as a book about finding a joyful second climb after your initial career path.
  01:19:12
• LionTree/Bourkoff invested in Malcolm Gladwell's audio company Pushkin Industries, per the 2021 year-end letter.
  01:20:46
• His favorite drink is the Mach2 at the Hemingway Bar at the Ritz in Paris (whiskey, chartreuse, ginger essence, ice); the bartender unexpectedly appeared at a New York event and made him one the night before the recording.
  01:36:36
• He was told in 2012 that launching a new independent bank was too late, just as Tim was told podcasting was too crowded by 2014-2016.
  01:24:37

Books, products and media the guest or host genuinely endorsed here — with the buy link.

Affiliate link — we may earn a commission at no extra cost to you.